185614-95-3

Upstream product

• 60656-87-3 benzyloxyacetoaldehyde 
• 156662-12-3 2-[1-(tert-Butyl-dimethyl-silanyloxy)-vinylsulfanyl]-pyridine 
• 4071-85-6 trimetylsilylketene 
• 506-96-7 Acetyl bromide 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 201230-82-2 carbon monoxide 
• 100-28-7 4-Nitrophenyl isocyanate 
• 75-36-5 acetyl chloride 

Downstream Products

• 261159-47-1 (4S)-4-(benzyloxymethyl)-oxetan-2-one 
• 252873-91-9 4-(R)-benzyloxymethyl-β-propiolactone 
• 853570-12-4 4-benzyloxymethyl-2-methyleneoxetane 
• 85418-23-1 (S)-1-O-benzyl-1,2,4-butanetriol 
• 279256-97-2 (R)-4-benzyloxy-3-(o-nitrobenzenesulfonamido)butanoic acid methyl ester 

Relevant academic research and scientific papers

An aluminum(III) picket fence phthalocyanine-based heterogeneous catalyst for ring-expansion carbonylation of epoxides

An effective heterogeneous catalyst for ring-expansion carbonylation of epoxides may have additional advantages over the homogeneous counterpart in terms of facile product separation and recyclability. A new Al(iii) picket fence phthalocyanine complex was synthesized and directly knitted using the Friedel-Crafts reaction to prepare a solid porous network, which was ultimately used to immobilize [Co(CO)4]- ions. The resulting heterogeneous catalyst, [Lewis acid]+[Co(CO)4]-, efficiently catalyzes the conversion of various epoxides into the corresponding β-lactones with high selectivity (99%) and stoichiometric conversion under mild reaction conditions, along with good functional group tolerance.

Highly Syndiotactic or Isotactic Polyhydroxyalkanoates by Ligand-Controlled Yttrium-Catalyzed Stereoselective Ring-Opening Polymerization of Functional Racemic β-Lactones

Reported herein is the first stereoselective controlled ROP of a specific family of racemic functional β-lactones, namely 4-alkoxymethylene-β-propiolactones (BPLORs). This process is catalyzed by an yttrium complex stabilized by a nonchiral tetradentate amino alkoxy bisphenolate ligand {ONOOR′2}2?, which features both a good activity and a high degree of control over the molar masses of the resulting functional poly(3-hydroxyalkanoate)s. A simple modification of the R′ substituents in ortho and para position on the ligand platform allows for a complete reversal from virtually pure syndioselectivity (Ps up to 0.91 with R′=cumyl) to very high isoselectivity (Pi up to 0.93 with R′=Cl), as supported by DFT insights. This is the first example of a highly isoselective ROP of a racemic chiral β-lactone.

Chromium(III) octaethylporphyrinato tetracarbonylcobaltate: A highly active, selective, and versatile catalyst for epoxide carbonylation

The development of a highly active and selective porphyrin-based epoxide carbonylation catalyst, [(OEP)Cr(THF)2][Co(CO)4] (1; OEP = octaethylporphyrinato; THF = tetrahydrofuran), is detailed. Complex 1 is a separated ion pair compose

A new multicomponent reaction catalyzed by a [Lewis acid] +[Co(CO)4]- catalyst: Stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO

The use of mechanistic information to develop a new, catalytic multicomponent reaction is described. The complex [(salph)AI(THF) 2]+[Co(CO)4]- (1, salph = N,N′-o-phenylenebis(3,5-di-tert-butyl-salicylideneimine), THF = tetrahydrofuran), which is known to carbonylate epoxides, aziridines, and β-lactones, was used to catalyze the synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO. Under optimized conditions, the reaction was both selective and high-yielding. 1,3-Oxazinane-2,4-diones were synthesized from a variety of epoxides and isocyanates, including some epoxides that do not undergo simple ring-expansion carbonylation. The best results were obtained using highly electrophilic isocyanates. The mechanism of the multicomponent reaction was investigated using labeling and stereochemistry, and the data obtained were consistent with the 1-catalyzed formation of β-lactone and 1,3-oxazinane-2,4-dione from a common intermediate.

Catalyzed acyl halide-aldehyde cyclocondensations. New insights into the design of catalytic cross aldol reactions

Substoichiometric quantities (2.5-20 mol%) of Al(SbF6)3 catalyze the di(isopropyl)ethylamine-mediated cyclocondensation of various acyl halides and enolizable aldehydes to afford β-lactones in good yields (58-93%). These reactions ar

Studies of the asymmetric [2+2] cycloaddition of silylketenes and aldehydes employing Ti-TADDOL catalysts

Ti-TADDOL catalysts provide good reactivity and moderate enantioselectivity in the asymmetric [2+2] cycloaddition of silyl ketenes and aldehydes. The effects of potential bidentate chelation of benzyloxy substituted aldehydes and of the steric size of the ketene silyl group were studied.

Studies of the tandem mukaiyama aldol-lactonization (TMAL) reaction: A concise and highly diastereoselective route to β-lactones applied to the total synthesis of the potent pancreatic lipase inhibitor, (-)-Panclicin D

A concise and highly diastereoselective route to β-lactones has been developed based on a tandem Mukaiyama aldol-lactonization employing thiopyridylsilylketene acetals and various aldehydes. (-) - Panclicin D, a potent pancreatic lipase inhibitor, was synthesized using this methodology. Recent optimization and extensions of this method are described which include variation of the silyl group and leaving group of the ketene acetal.